Chappelle is popular with Edgelords Of A Certain Age because he was their Richord Pryor when they were in high school/early college. Their parents were offended, the jokes were transgressive, he was on basic cable, and young adult males are presumed to be assholes until proven otherwise so the punching down humor and basic cruelty of it all was forgiven.

Dane Cook was very popular at the same time, as was Bill Maher. Dane Cook, of course, being an angry punching-down version of Steve Martin and Bill Maher being an angry punching-down version of George Carlin. Dane Cook was eliminated by the comics themselves, who pointed out (rightly) that much of his material was lifted from Louis CK and Joe Rogan, whose stars ascended as the edgelords stopped caring about the funny and homed in on the offense as serious thought leaders of the New Right. Bill Maher followed a similar trajectory where "being funny" matters a whole lot less than "annoy my liberal coworkers."

Dave Chappelle, for his part, pretty much abandoned the world when he realized that his schtick wasn't making people laugh the way it used to, and then came back when he realized that Edgelords Of A Certain Age will happily laugh at mediocre humor if it targets the same thing they hate. It's amusing to me that the same people who will die on a hill professing that Dave Chappelle is being "cancelled" will freely and happily admit that Dennis Miller just isn't funny without recognizing that audiences are allowed more leeway to laugh at a misogynistic black man than they are a misogynistic white man.

It's really this simple: you're allowed puerile humor until your early '20s, at which point normies gain a little sophistication. The Joe Rogan/Louis CK/Dave Chappelle/Dane Cook/Bill Maher crowd has never advanced beyond puerile humor. Those under the age of 25, however, have an entirely different set of people they want to laugh at, and "the vulnerable" are not among them. So you stop writing jokes for puerile kids and instead write jokes for the Alex Jones crowd.